Why Did Leia Seek Out Obiwan Kenobi Now?

As I was falling asleep last night, after having watched a Star Wars Rebels, I had a sudden thought: Why now? The new movie Rogue One will end where Star Wars: A New Hope begins, with the delivery of the Death Star plans.

But my question is this: Why was Princess Leia delivering the plans to Obiwan Kenobi. From the trailer for Rogue One, it’s very clear that it is the Rebellion, lead by Mon Mothma, who sends Jyn Erso and her team to retrieve the Death Star plans. So why aren’t the plans delivered back to Mon Mothma? At the beginning of A New Hope, Leia’s ship—which was presumably at the battle where the plans were stolen—is racing back to Alderaan. As the opening crawl writes:

It is a period of civil war. Rebel spaceships, striking from a hidden base, have won their first victory against the evil Galactic Empire. During the battle, Rebel spies managed to steal secret plans to the Empire’s ultimate weapon, the Death Star, an armored space station with enough power to destroy an entire planet. Pursued by the Empire’s sinister agents, Princess Leia races home aboard her starship, custodian of the stolen plans that can save her people and restore freedom to the galaxy…

So, intercepted by the Imperial Star Destroyer, Leia instead makes for Tatooine. Why? In her hologram, she tells Obiwan that she was sent by Bail Organa to get him to help in the Rebellion.

General Kenobi, years ago you served my father in the Clone Wars. Now he begs you to help him in his struggle against the Empire. I regret that I am unable to present my father’s request to you in person, but my ship has fallen under attack and I’m afraid my mission to bring you to Alderaan has failed. I have placed information vital to the survival of the Rebellion into the memory systems of this R2 unit. My father will know how to retrieve it. You must see this droid safely delivered to him on Alderaan. This is our most desperate hour. Help me, Obi-Wan Kenobi, you’re my only hope.

And thus my question:

Why now?

Update: Having watched Rogue One after writing this, my question has been answered to some degree, but not completely.

Based on the message, we can assume that Bail Organa told Leia that after she got the Death Star plans, she should bring them to him on Alderaan.1 So why did Bail think it was the right time for Obiwan to come out of hiding. Remember, Obiwan and Organa split up Anakin’s twins to keep them safe and presumably to keep one in hiding even if Vader found the other. And from Obiwan’s words to Luke here—“You must learn the ways of the Force if you’re to come with me to Alderaan”—that some pre-condition for ending that separation had been fulfilled.

So what was it about the Death Star plans that fulfilled that condition? Remember, they did not know for sure that there was a vulnerability (or did they?). But at the least the Rebellion had suddenly moved out of the shadows into a full-fledged military action. Was this the pre-agreed condition for the Skywalker twins to be revealed?

Let’s theorize on what would have happened had Vader not intercepted Leia. She would have arrived on Tatooine and gone to Kenobi’s hut. There she would deliver her message. Obiwan would then have collected Luke, introduced him to Leia, and off they would fly to Alderaan. From there, they would have traveled with Sen. Organa to Yavin where the Rebels would find the Death Star’s flaw and plans would have gone into motion to destroy it. Meanwhile, what of Luke and Leia? Would they have gone into training with Obiwan and Yoda to become Jedi? Interesting to speculate.

I think it was the very existence of the Death Star that signaled that it was time. The Death Star would have taken most of the nearly two decades of the Empire’s existence to that time to build. It’s completion would have moved the Empire into a new phase of absolute oppression. Nothing would stand in the way of the Emperor’s ability to crush any resistance and impose his will.

The Jedi had been all but obliterated (although I like my head canon where Asohka and Kanan and Ezra are out there in hiding someplace, waiting to come forward after the events of Return of the Jedi), but now is the time for the new Jedi Order to rise up against the Sith! I could see Obiwan and Yoda working together to train Luke and Leia for the day they would confront their father and his master. It’s an interesting thought experiment.

But it’s also interesting to realize that one way or another Luke’s time on a small, backwater planet and Leia’s existence as an Imperial Senator were coming to an end.

Now, I only have to watch Rogue One this week and see how much it changes my presumptions and assumptions above. I’ll check back in.

This is all contingent on what happens in Rogue One, of course, but this is pretty clear from what happens in A New Hope. ↩